With the long-rumoured Oblivion remaster allegedly dropping tomorrow (unless Todd Howard is playing 4D chess again), it’s time to revisit one of the most beloved RPGs of all time. While The Elder Scrolls IV: Oblivion is famous for its main questline involving portals to hell, Daedric princes, and the ever-enthusiastic Martin Septim, it’s the side quests that truly gave the game its heart—and frequent moments of hilarious weirdness.

From shady dealings in Skingrad to trippy dreamscapes in Bruma, Oblivion, along with its expansions Shivering Isles and Knights of the Nine – both of which are said to be included in the remaster – offered some of the most memorable and creative diversions in RPG history. Here’s my top ten best side quests you absolutely shouldn’t skip (again).

1. Whodunit?

Location: Dark Brotherhood Questline
How to Start: Join the Dark Brotherhood by killing an innocent NPC and sleeping. Given by Ocheeva in Cheydinhal.
Why It’s Great: It’s “Clue,” if you were the killer and also extremely committed to your craft. Locked in a mansion with five guests, your task is simple: murder everyone without raising suspicion. It’s a delightfully wicked sandbox of stealth, manipulation, and social deduction—and arguably the most fun you’ll ever have committing serial murder.

2. The Ultimate Heist

Location: Thieves Guild Final Quest
How to Start: Complete the Thieves Guild questline.
Why It’s Great: Stealing an Elder Scroll isn’t just any Tuesday night crime—it’s the ultimate flex. This capstone to the Thieves Guild is a complex, high-stakes infiltration of the Imperial Palace. It’s got riddles, traps, and some very tense sneaking. Honestly, you’ll feel like a medieval Ocean’s Eleven (if Danny Ocean were a Khajiit in a hood).

3. A Brush With Death

Location: Cheydinhal
How to Start: Speak to Tivela Lythandas in Cheydinhal to find her missing painter husband.
Why It’s Great: You literally jump into a painting. The game turns into an oil-painted dreamscape, where you battle goblin-like creatures with a magical paintbrush. It’s whimsical, weird, and proves Oblivion was never afraid to let its freak flag fly. Plus, it’s probably the only quest in gaming where Bob Ross could have been the final boss. Remember, there are no mistakes, just happy little stabbings.

4. Through A Nightmare, Darkly

Location: Bruma
How to Start: Speak with Kurdan gro-Dragol at the Jerall View Inn.
Why It’s Great: You dive into a man’s troubled dreams to rescue him, wandering through a surreal nightmare landscape full of haunting imagery and metaphorical monsters. It’s basically Inception, except instead of a totem, you’ve got a sword and no one explains the plot five times. And the soundtrack isn’t composed of BRAAAMs.

5. Everything In Its Place (Shivering Isles Expansion)

Location: Crucible, Shivering Isles
How to Start: Speak with the OCD-riddled Dunmer, Shelden, in Crucible.
Why It’s Great: The Shivering Isles is full of bizarre citizens, but few are as hilariously obsessive as Shelden. You’re tasked with retrieving items he believes were stolen—except they weren’t, and he just doesn’t like them being out of place. It’s a textbook case of madness, but the kind that ends in laughter, not horror.

6. Paranoia

Location: Skingrad
How to Start: Talk to Glarthir, a suspicious Wood Elf lurking around town.
Why It’s Great: This quest is a descent into delusion—only it’s someone else’s. Glarthir thinks the whole town is conspiring against him, and he wants your help to prove it. Do you aid his madness or turn him in? It’s one of the funniest, darkest, and most unpredictable quests in the game. Bonus: you’ll never look at a Skingrad citizen the same again.

7. The Collector

Location: Imperial City, Talos Plaza District
How to Start: Speak to Umbacano, a charmingly shady Altmer noble.
Why It’s Great: A long treasure hunt across Ayleid ruins that eventually devolves into a classic case of “rich guy lies to adventurer.” It mixes exploration, archaeology, and betrayal in perfect Elder Scrolls fashion. Plus, Umbacano’s smug voice alone makes the whole thing worth it.

8. The Fork Of Horripilation (Shivering Isles Expansion)

Location: Bliss, New Sheoth
How to Start: Speak to Big Head, a mad Argonian with an unhealthy obsession, in Bliss.
Why It’s Great: Big Head has lost his precious Fork of Horripilation, and he needs it back. Not wants—needs. You’re tasked with retrieving this utterly useless piece of cutlery, because clearly, the fate of the Isles depends on it. The quest is a masterclass in ridiculousness, wrapped in layers of madness, and capped off with one of the most bizarre characters in the game. It’s wonderfully pointless in all the right ways—exactly what you’d expect from Sheogorath’s realm.

9. The Siren’s Deception

Location: Anvil
How to Start: Speak to Maelona outside the Count’s Arms in Anvil.
Why It’s Great: A trio of suspiciously friendly women lure you to a secluded farmhouse, and—surprise!—you’re ambushed by a gang of bandits dressed like they just walked off the set of Skyrim: Love Island. This quest is part cautionary tale, part crime drama, and all hilariously over-the-top. The setup is cheesy, the twist is absurd, and the loot isn’t bad either. It’s one of those rare moments where Oblivion winks at you and says, “Yeah, we know.”

10. Mazoga The Orc

Location: Leyawiin
How to Start: Speak to Count Marius Caro in Leyawiin Castle.
Why It’s Great: Mazoga seems like your typical grumpy Orc, but beneath the tough exterior is a surprisingly noble character arc. Help her become a true knight in an unexpectedly touching series of quests. It’s a great reminder that Oblivion was never afraid to challenge fantasy tropes—even if it did it with all the subtlety of a warhammer to the face.